Regiodirecting effects in difunctionalised tricarbonyl[(1,2,3,4,5-η)-cyclohexadienyl]iron(1+) salts: building blocks for alkaloids

G. Richard Stephenson, Ian M. Palotai

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Electrophilic tricarbonyl[(1,2,3,4,5-η)-cyclohexadienyl]iron(1+) salts that incorporate methoxy and 2-ethanoyl ester substituents have been prepared, and the regiochemistry of their reactions with nucleophiles in arylation reactions has been examined using the model nucleophile diphenylzinc. The 1-carbomethoxymethyl-2-methoxy salt 1 reacts selectively by the ω addition pathway, but the 2-carbomethoxymethyl-3-methoxy salt 9 gave a 6:1 mixture of ω and α addition products. The 1-carbomethoxymethyl-2-methoxy regioisomer 1 was prepared in >95% purity without recourse to chromatography and shows the correct regiocontrol for use as a starting material in organoiron-mediated routes to alkaloids such as lycorine and parkacine.
Original languageEnglish
Pages (from-to)123-127
Number of pages5
JournalTetrahedron Letters
Issue number2
Early online date6 Oct 2012
Publication statusPublished - 9 Jan 2013

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